Rain or shine, indoors or outdoors, Rooftop Films kicks off tonight with a program of live music and short films on the L.E.S., either indoors our outdoors, and continues tomorrow night with the world premiere of Freeloader, by the NYC filmmaker Zachary Raines, shot in and around Brooklyn.

For anyone who saw Ramin Serry’s Loveless at the reRun earlier this year, the setup will be familiar, with a differently tailored demographic cut: Frank (Kyle Espeleta), a scruffy, indeterminately twenty-or-thirtysomething, is one of those fuck-ups who coasts by on the occasional spark of the charisma his friends remember so fondly; as in the earlier film, he falls in with a mysterious, moneyed, socially awkward Faustian enabler.

Frank, mostly too drunk to riff, makes the circuit of bar to friend’s couch to ex’s futon and back around again; the scenes, shot among friends, are intimate and caustically performed—so far, so familiar indie movie about a questionably sympathetic possible directorial stand-in. But Freeloader becomes a not unserious moral dilemma as world-class moocher Frank plays on the utterly unself-aware loneliness of banker, hi-rise condo-dweller, and aspiring stand-up comic Ray, played by Jesse Wakeman with a rubbery, transparently desperate rictus grimace. The turning point of their relationship and the film’s showstopper, such as it is, is a not quite squirmingly terrible stand-up routine Ray performs at Hank’s Saloon (where filmmaker Raines cameos as another bad stand-up comic, riffing on airline peanuts. What’s the deal with them?).